Fragmentation of nitrone triflates to 9-membered rings

John A. Murphy, Mohan Mahesh, Gary McPheators, R. Vijaya Anand, Thomas M. McGuire, Robert Carling, Alan R. Kennedy

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)


A new fragmentative rearrangement of nitrone derivatives to form 9-membered rings is reported. The fragmentations are triggered when nitrones are treated with triflic anhydride; a C-C bond antiperiplanar to the cleaving N-O bond is activated either by an oxygen lone pair or by an electron-rich aromatic ring. In the former case, further cyclization of the 9-membered intermediate leads to a rearranged condensed ring system, but when triggered by arenes, 9-membered ring amides are isolated.

Original languageEnglish
Pages (from-to)3233-3236
Number of pages4
JournalOrganic Letters
Issue number17
Publication statusPublished - 16 Aug 2007


  • nitrone triflates
  • cyclization
  • amides


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